354153-47-2

Upstream product

• 769-25-5 2,4,6-trimethylstyrene 
• 34867-87-3 spirocyclobutylmalonoyl peroxide 

Downstream Products

• 173171-08-9 (R)-1-(2,4,6-trimethylphenyl)-2-(1-piperidinyl)ethanol 
• 354153-59-6 (S)-2-Hydroxy-N-[(S)-2-hydroxy-1-(2,4,6-trimethyl-phenyl)-ethyl]-2-phenyl-acetamide 
• 354153-55-2 (S)-2-Hydroxy-N-[(R)-2-hydroxy-1-(2,4,6-trimethyl-phenyl)-ethyl]-2-phenyl-acetamide 
• 924265-80-5 (R)-2-amino-2-(2,4,6-trimethylphenyl)ethanol 
• 354153-49-4 (+/-)-2-amino-2-(2,4,6-trimethylphenyl)ethanol 

Relevant academic research and scientific papers

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

Metal-free dihydroxylation of alkenes using cyclobutane malonoyl peroxide

Cyclobutane malonoyl peroxide (7), prepared in a single step from the commercially available diacid 6, is an effective reagent for the dihydroxylation of alkenes. Reaction of a chloroform solution of 7 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (30-84%). With 1,2-disubstituted alkenes, the reaction proceeds with syn-selectivity (3:1 → 50:1). A mechanism consistent with experimental findings is proposed, which is supported by deuterium and oxygen labeling studies and explains the stereoselectivity observed. Alternative reaction pathways that are dependent on the structure of the starting alkene are also described leading to the synthesis of allylic alcohols and γ-lactones.

Alkene syn dihydroxylation with malonoyl peroxides

Cyclopropyl malonoyl peroxide (1), which can be prepared in a single step from the commercially available diacid, is an effective reagent for the dihydroxylation of alkenes. Reaction of 1 with an alkene in the presence of 1 equiv of water at 40 °C followed by alkaline hydrolysis leads to the corresponding diol (40-93%). With 1,2-disubstituted alkenes, the reaction proceeds with syn selectivity (3:1 to >50:1). A mechanism consistent with the experimental findings that is supported by oxygen-labeling studies is proposed.

New uses for the Burgess reagent in chemical synthesis: Methods for the facile and stereoselective formation of sulfamidates, glycosylamines, and sulfamides

Although the Burgess reagent (methoxycarbonylsulfamoyltriethylammonium hydroxide, inner salt) has found significant use in chemical synthesis as a dehydrating agent, almost no work has been directed towards its potential in other synthetic applications. As this article will detail, we have found that the Burgess reagent is remarkably effective at accomplishing a number of non-dehydrative synthetic tasks when applied to appropriate substrates, such as the formation of sulfamidates from 1,2-diols or epoxyalcohols, α- and β-glycosylamines from carbohydrates, and cyclic sulfamides from 1,2-aminoalcohols. Beyond delineating the power of these new reaction manifolds, we also describe the construction of a group of alternative Burgess-type reagents that extends the scope of these new reactions even further.

An effective and useful synthesis of enantiomerically enriched arylglycinols

A two-step synthesis of racemic arylglycinols, together with a simple and straightforward methodology for their resolution, is described. This method constitutes a practical means of preparing racemic and optically pure electron-rich or electron-poor subs